US4374989A - Process for the manufacture of dianthraquinonyl-N,N'-dihydroazine - Google Patents
Process for the manufacture of dianthraquinonyl-N,N'-dihydroazine Download PDFInfo
- Publication number
- US4374989A US4374989A US06/293,985 US29398581A US4374989A US 4374989 A US4374989 A US 4374989A US 29398581 A US29398581 A US 29398581A US 4374989 A US4374989 A US 4374989A
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- hydrazine
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- reaction
- reaction mixture
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- 238000000034 method Methods 0.000 title claims abstract description 28
- 229910052757 nitrogen Inorganic materials 0.000 title claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 4
- 239000011541 reaction mixture Substances 0.000 claims abstract description 28
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 23
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 20
- YCANAXVBJKNANM-UHFFFAOYSA-N 1-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] YCANAXVBJKNANM-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 230000001476 alcoholic effect Effects 0.000 claims abstract description 8
- 239000000470 constituent Substances 0.000 claims abstract description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 12
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims description 12
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 12
- 238000009835 boiling Methods 0.000 claims description 4
- -1 hydroxylamine compound Chemical class 0.000 claims description 4
- BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- ZGCHATBSUIJLRL-UHFFFAOYSA-N hydrazine sulfate Chemical compound NN.OS(O)(=O)=O ZGCHATBSUIJLRL-UHFFFAOYSA-N 0.000 claims description 3
- 229910000377 hydrazine sulfate Inorganic materials 0.000 claims description 3
- LIAWOTKNAVAKCX-UHFFFAOYSA-N hydrazine;dihydrochloride Chemical compound Cl.Cl.NN LIAWOTKNAVAKCX-UHFFFAOYSA-N 0.000 claims description 3
- VGYYSIDKAKXZEE-UHFFFAOYSA-L hydroxylammonium sulfate Chemical compound O[NH3+].O[NH3+].[O-]S([O-])(=O)=O VGYYSIDKAKXZEE-UHFFFAOYSA-L 0.000 claims description 3
- 229910000378 hydroxylammonium sulfate Inorganic materials 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- DVHXJLRODLTJOD-UHFFFAOYSA-N aminoazanium;bromide Chemical compound Br.NN DVHXJLRODLTJOD-UHFFFAOYSA-N 0.000 claims description 2
- VJRITMATACIYAF-UHFFFAOYSA-N benzenesulfonohydrazide Chemical compound NNS(=O)(=O)C1=CC=CC=C1 VJRITMATACIYAF-UHFFFAOYSA-N 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- WHRIKZCFRVTHJH-UHFFFAOYSA-N ethylhydrazine Chemical compound CCNN WHRIKZCFRVTHJH-UHFFFAOYSA-N 0.000 claims description 2
- IIXGBDGCPUYARL-UHFFFAOYSA-N hydroxysulfamic acid Chemical compound ONS(O)(=O)=O IIXGBDGCPUYARL-UHFFFAOYSA-N 0.000 claims description 2
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 claims description 2
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims description 2
- 229940067157 phenylhydrazine Drugs 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 238000010923 batch production Methods 0.000 claims 1
- 150000002443 hydroxylamines Chemical class 0.000 abstract description 6
- 150000001298 alcohols Chemical class 0.000 abstract description 5
- 239000007795 chemical reaction product Substances 0.000 description 14
- 239000000725 suspension Substances 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000012065 filter cake Substances 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000019239 indanthrene blue RS Nutrition 0.000 description 1
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/44—Azines of the anthracene series
- C09B5/46—Para-diazines
- C09B5/48—Bis-anthraquinonediazines (indanthrone)
Definitions
- the present invention provides a process for the manufacture of dianthraquinonyl-N,N'-dihydroazine, which comprises reacting 1-nitroanthraquinone in mixtures of water, alcohols and alkali metal hydroxides at elevated temperature with hydrazine or hydroxylamine compounds, subsequently removing the alcoholic constituents from the reaction mixture, adding dimethyl sulfoxide and, if desired, further amounts of alkali metal hydroxides, and bringing the reaction to completion at elevated temperature.
- the reaction of 1-nitroanthraquinone with hydrazine or hydroxylamine compounds is advantageously carried out above room temperature.
- the reaction temperature can vary within a wide range compatible with the reactants and is preferably between room temperature and the boiling temperature of the reaction mixture.
- the reaction of 1-nitroanthraquinone with hydrazine or hydroxylamine compounds is carried out at the boiling temperature of the reaction mixture with reflux cooling.
- the subsequent removal of the alcoholic constituents from the reaction mixture can be accomplished by known methods, for example by distillation (azeotropic distillation) or, if desired, by extraction.
- the alcoholic constituents are removed from the reaction mixture preferably by distillation.
- reaction is brought to completion, likewise at elevated temperature. Reaction temperatures between 80° and 140° are normally chosen. Preferably, the reaction is brought to completion at 120° to 125° C. In the final stage of the process, it is advantageous to introduce air into the reaction mixture while heating the latter.
- Suitable alkali metal hydroxides are in particular sodium and potassium hydroxide or also mixtures of both.
- suitable alcohols are: methanol, ethanol, propanol, isopropanol, n-butanol, benzyl alcohol.
- Several alcohols can also be used simultaneously in the reaction mixture.
- the ratio of water to alcohols can vary; preferably equal parts of water and alcohol are employed.
- a preferred embodiment of the process of this invention consists in carrying out the reaction of 1-nitroanthraquinone with hydrazine or hydroxylamine compounds in mixtures of water, methanol or ethanol and potassium hydroxide.
- the amount of alkali metal hydroxides added is two to three times greater than the amount added initially.
- the amount of dimethyl sulfoxide employed is preferably about as great as the amount of water and alcohol initially used.
- hydrazine and hydroxylamine compounds are: hydrazine, hydrazine hydrate, methyl hydrazine, ethyl hydrazine, phenyl hydrazine, hydrazinium chloride, hydrazinium dichloride, hydrazinium sulfate, hydrazinium bromide, benzenesulfonyl hydrazide, hydroxylamine, hydroxylamine hydrochloride, hydroxylammonium sulfate, hydroxylaminesulfonic acid.
- hydrazine or hydroxylamine hydrochloride is used.
- reaction products can be isolated from the reaction mixture in known manner.
- the reaction mixture is cooled to room temperature, then diluted with water, partially neutralised with a mineral acid, and filtered.
- the filter cake is washed with hot water and then dried.
- reaction mixture is then cooled to room temperature, poured into about 2 liters of water and partially neutralised with 300 ml of 4 N hydrochloric acid (pH 9 to 10).
- the reaction mixture is then filtered.
- the filter cake is freed from salt and by-products by washing it with hot water, and dried at 70°-80° C. Yield: 20.3 parts (91.8% of theory).
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for the manufacture of dianthraquinonyl-N,N'-dihydroazine, which comprises reacting 1-nitroanthraquinone in mixtures of water, alcohols and alkali metal hydroxides at elevated temperature with hydrazine or hydroxylamine compounds, subsequently removing the alcoholic constituents from the reaction mixture, adding dimethyl sulfoxide, and, if desired, further amounts of alkali metal hydroxides, and bringing the reaction to completion at elevated temperature.
Description
This application is a continuation of application Ser. No. 149,125, filed May 8, 1980, which application is in turn a continuation of application Ser. No. 33,406, filed Apr. 6, 1979 (both now abandoned).
The present invention provides a process for the manufacture of dianthraquinonyl-N,N'-dihydroazine, which comprises reacting 1-nitroanthraquinone in mixtures of water, alcohols and alkali metal hydroxides at elevated temperature with hydrazine or hydroxylamine compounds, subsequently removing the alcoholic constituents from the reaction mixture, adding dimethyl sulfoxide and, if desired, further amounts of alkali metal hydroxides, and bringing the reaction to completion at elevated temperature.
The reaction of 1-nitroanthraquinone with hydrazine or hydroxylamine compounds is advantageously carried out above room temperature. The reaction temperature can vary within a wide range compatible with the reactants and is preferably between room temperature and the boiling temperature of the reaction mixture. In particular, the reaction of 1-nitroanthraquinone with hydrazine or hydroxylamine compounds is carried out at the boiling temperature of the reaction mixture with reflux cooling. The subsequent removal of the alcoholic constituents from the reaction mixture can be accomplished by known methods, for example by distillation (azeotropic distillation) or, if desired, by extraction. The alcoholic constituents are removed from the reaction mixture preferably by distillation. After addition of dimethyl sulfoxide and, if desired, further amounts of alkali metal hydroxides, the reaction is brought to completion, likewise at elevated temperature. Reaction temperatures between 80° and 140° are normally chosen. Preferably, the reaction is brought to completion at 120° to 125° C. In the final stage of the process, it is advantageous to introduce air into the reaction mixture while heating the latter.
Suitable alkali metal hydroxides are in particular sodium and potassium hydroxide or also mixtures of both. Examples of suitable alcohols are: methanol, ethanol, propanol, isopropanol, n-butanol, benzyl alcohol. Several alcohols can also be used simultaneously in the reaction mixture. The ratio of water to alcohols can vary; preferably equal parts of water and alcohol are employed. In addition, it is preferable to use about equal parts of alkali metal hydroxide and 1-nitroanthraquinone and, based on the amount of this latter, about twice the molar amount of hydrazine or hydroxylamine compound.
A preferred embodiment of the process of this invention consists in carrying out the reaction of 1-nitroanthraquinone with hydrazine or hydroxylamine compounds in mixtures of water, methanol or ethanol and potassium hydroxide.
After removal of the alcoholic constituents from the reaction mixture, it is advantageous to add further amounts of alkali metal hydroxides to the reaction mixture. Preferably, the amount of alkali metal hydroxides added is two to three times greater than the amount added initially. The amount of dimethyl sulfoxide employed is preferably about as great as the amount of water and alcohol initially used.
Examples of hydrazine and hydroxylamine compounds are: hydrazine, hydrazine hydrate, methyl hydrazine, ethyl hydrazine, phenyl hydrazine, hydrazinium chloride, hydrazinium dichloride, hydrazinium sulfate, hydrazinium bromide, benzenesulfonyl hydrazide, hydroxylamine, hydroxylamine hydrochloride, hydroxylammonium sulfate, hydroxylaminesulfonic acid. Preferably, hydrazine or hydroxylamine hydrochloride is used.
The reaction products can be isolated from the reaction mixture in known manner. For example, the reaction mixture is cooled to room temperature, then diluted with water, partially neutralised with a mineral acid, and filtered. The filter cake is washed with hot water and then dried.
The reaction product, dianthraquinonyl-N,N'-dihydroazine (indanthrone, C.I. Vat Blue, C.I. No. 69800), is a valuable vat dye. It has the formula
The invention is illustrated by the following Examples, in which the parts and percentages are by weight unless otherwise indicated. The relationship of parts by weight to parts by volume is the same as that of grams to milliliters.
25.3 parts of 1-nitroanthraquinone are suspended at room temperature in 80 parts of methanol. Then 90 parts of water, 26 parts of solid potassium hydroxide and 8 parts of hydrazine hydrate are added. The suspension is refluxed for 3 hours and the methanol is then distilled off. Then 64 parts of solid potassium hydroxide followed by 70 parts of dimethyl sulfoxide are added cautiously to the suspension. The suspension is heated to 120°-125° C. and kept for 11/2 hours at this temperature. The reaction mixture is subsequently kept for a further 3 hours at 120°-125° C., during which time air is introduced. The reaction mixture is then cooled to room temperature, poured into about 2 liters of water and partially neutralised with 300 ml of 4 N hydrochloric acid (pH 9 to 10). The reaction mixture is then filtered. The filter cake is freed from salt and by-products by washing it with hot water, and dried at 70°-80° C. Yield: 20.3 parts (91.8% of theory).
The same end product is obtained in a yield of 20 parts by repeating the procedure of Example 1 using ethanol instead of methanol.
The same end product is obtained in a yield of 20.2 parts by repeating the procedure of Example 1 using 10 parts of hydroxylamine hydrochloride instead of 8 parts of hydrazine hydrate.
The same end product is obtained in a yield of 20 parts by repeating the procedure of Example 1 using ethanol instead of methanol and 10 parts of hydroxylamine hydrochloride instead of 8 parts of hydrazine hydrate.
The same end product is obtained in a yield of 20 parts by repeating the procedure of Example 1 using 28 parts of hydrazinium sulfate instead of 8 parts of hydrazine hydrate.
The same end product is obtained in a yield of 20.1 parts by repeating the procedure of Example 1 using 15 parts of hydrazinium chloride instead of 8 parts of hydrazine hydrate.
The same end product is obtained in a yield of 20.2 parts by repeating the procedure of Example 1 using 23 parts of hydrazinium dichloride instead of 8 parts of hydrazine hydrate.
The same end product is obtained in a yield of 20 parts by repeating the procedure of Example 1 using 15 parts of hydroxylammonium sulfate instead of 8 parts of hydrazine hydrate.
The same end product is obtained in a yield of 20.2 parts by repeating the procedure of Example 1 using isopropanol instead of methanol.
The same end product is obtained in a yield of 20 parts by repeating the procedure of Example 1 using propanol instead of methanol.
25.3 parts of 1-nitroanthraquinone are suspended at room temperature in 150 parts of methanol. Then 15 parts of solid potassium hydroxide and 8 parts of hydrazine hydrate are added. The suspension is refluxed for 3 hours and the methanol is then distilled off. Then 90 ml of water, 75 parts of solid potassium hydroxide followed by 70 parts of dimethyl sulfoxide are added cautiously to the reaction mixture. The suspension is heated to 120°-125° C. and kept for 11/2 hours at this temperature. The reaction mixture is subsequently kept for a further 3 hours at 120°-125° C., during which time air is introduced. The reaction mixture is then cooled to room temperature and poured into about 1 liter of water. The reaction mixture is then filtered. The filter cake is freed from salt and by-products by washing it with hot water, and dried at 70°-80° C. Yield: 20 parts (91.5% of theory).
The same end product is obtained in a yield of 20 parts by repeating the procedure of Example 11 using ethanol instead of methanol.
The same end product is obtained in a yield of 20.2 parts by repeating the procedure of Example 11 using isopropanol instead of methanol.
The same end product is obtained in a yield of 20 parts by repeating the procedure of Example 11 using propanol instead of methanol.
25.3 parts of 1-nitroanthraquinone are suspended at room temperature in 160 parts of water. Then 26 parts of solid potassium hydroxide and 8 parts of hydrazine hydrate are added. The suspension is refluxed for 3 hours and 70 ml of water are then distilled off. Then 64 parts of solid potassium hydroxide followed by 70 parts of dimethyl sulfoxide are added cautiously to the suspension. The suspension is heated to 120°-125° C. and kept for 11/2 hours at this temperature. The reaction mixture is subsequently kept for a further 3 hours at 120°-125° C., during which time an oxygen/nitrogen mixture with 8% by volume of oxygen is introduced. The reaction mixture is then cooled to room temperature and poured into about 1 liter of water. The reaction mixture is then filtered. The filter cake is freed from salt and by-products by washing it with hot water, and dried at 70°-80° C. Yield: 20 parts (91.5% of theory).
Claims (11)
1. A one-batch process for the manufacture of dianthraquinonyl-N,N'-dihydroazine, which comprises reacting 1-nitroanthraquinone in a mixture of (a) water or a mixture of water and at least one alcohol and (b) an alkali metal hydroxide or a mixture of alkali metal hydroxides at a temperature of between room temperature and the boiling temperature of the reaction mixture with hydrazine, hydrazine hydrate, methyl hydrazine, ethyl hydrazine, phenyl hydrazine, hydrazinium chloride, hydrazinium dichloride, hydrazinium sulfate, hydrazinium bromide, benzenesulfonyl hydrazine, hydroxylamine, hydroxylamine hydrochloride, hydroxylammonium sulfate or hydroxylamine sulfonic acid, subsequently removing any alcoholic constituents present from the reaction mixture, adding to the reaction mixture dimethyl sulfoxide or dimethyl sulfoxide and a further amount of alkali metal hydroxide, and bringing the reaction to completion at a temperature between 80° and 140° C.
2. A process according to claim 1, wherein the reaction of 1-nitroanthraquinone with hydrazine or hydroxylamine compound as defined in claim 1 is carried out at the boiling temperature of the reaction mixture with reflux cooling.
3. A process according to either of claim 1 or claim 2, wherein any alcoholic constituents present are removed from the reaction mixture by distillation.
4. A process according to either of claim 1 or claim 2, wherein the reaction is brought to completion in the temperature range of between 120° to 125° C.
5. A process according to either of claim 1 or claim 2, wherein the reaction is brought to completion while introducing air.
6. A process according to either of claim 1 or claim 2, wherein about equal amounts of water and alcohol are used.
7. A process according to either of claim 1 or claim 2, wherein there are used about equal parts of alkali metal hydroxide and 1-nitroanthraquinone, and, based on the 1-nitroanthraquinone, about twice the molar amount of the hydrazine or hydroxylamine compound as defined in claim 1.
8. A process according to either of claim 1 or claim 2, wherein the reaction of 1-nitroanthraquinone with hydrazine or hydroxylamine compound as defined in claim 1 is carried out in a mixture of water, methanol or ethanol and potassium hydroxide.
9. A process according to either of claim 1 or claim 2, wherein two to three times the initial amount of alkali metal hydroxide is added after removal of any alcoholic constituents present from the reaction mixture.
10. A process according to either of claim 1 or claim 2, wherein dimethyl sulfoxide is employed in an amount about as great as the amount of water and alcohol initially used.
11. A process according to either of claim 1 or claim 2, wherein hydrazine hydrate or hydroxylamine hydrochloride is used.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH496078A CH634861A5 (en) | 1978-05-08 | 1978-05-08 | METHOD FOR PRODUCING DIANTHRACHINONYL-N, N'-DIHYDROAZINE. |
| CH4960/78 | 1978-05-08 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06149125 Continuation | 1980-05-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US4374989A true US4374989A (en) | 1983-02-22 |
Family
ID=4285517
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/293,985 Expired - Fee Related US4374989A (en) | 1978-05-08 | 1981-08-18 | Process for the manufacture of dianthraquinonyl-N,N'-dihydroazine |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4374989A (en) |
| JP (1) | JPS54146830A (en) |
| CH (1) | CH634861A5 (en) |
| DE (1) | DE2918262A1 (en) |
| FR (1) | FR2425464A1 (en) |
| GB (1) | GB2020682B (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3242182A (en) * | 1962-04-16 | 1966-03-22 | Allied Chem | Indanthrone process |
| US3268532A (en) * | 1962-12-04 | 1966-08-23 | Cassella Farbwerke Mainkur Ag | Process for producing dyestuffs of the anthraquinoneazine series |
| US4016182A (en) * | 1973-05-28 | 1977-04-05 | Sandoz Ltd. | Process for the production of aminoanthraquinone compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1376198A (en) * | 1963-12-03 | 1964-10-23 | Cassella Farbwerke Mainkur Ag | Process for the preparation of dyes of the anthraquinone-azine series |
-
1978
- 1978-05-08 CH CH496078A patent/CH634861A5/en not_active IP Right Cessation
-
1979
- 1979-05-07 FR FR7911436A patent/FR2425464A1/en active Granted
- 1979-05-07 DE DE19792918262 patent/DE2918262A1/en not_active Withdrawn
- 1979-05-08 JP JP5534979A patent/JPS54146830A/en active Pending
- 1979-05-08 GB GB7915840A patent/GB2020682B/en not_active Expired
-
1981
- 1981-08-18 US US06/293,985 patent/US4374989A/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3242182A (en) * | 1962-04-16 | 1966-03-22 | Allied Chem | Indanthrone process |
| US3268532A (en) * | 1962-12-04 | 1966-08-23 | Cassella Farbwerke Mainkur Ag | Process for producing dyestuffs of the anthraquinoneazine series |
| US4016182A (en) * | 1973-05-28 | 1977-04-05 | Sandoz Ltd. | Process for the production of aminoanthraquinone compounds |
Non-Patent Citations (1)
| Title |
|---|
| Mosley, Chem. Ind. (London), (1959), pp. 1348-1349. * |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2020682A (en) | 1979-11-21 |
| FR2425464A1 (en) | 1979-12-07 |
| DE2918262A1 (en) | 1979-11-15 |
| CH634861A5 (en) | 1983-02-28 |
| JPS54146830A (en) | 1979-11-16 |
| GB2020682B (en) | 1982-11-10 |
| FR2425464B1 (en) | 1981-12-04 |
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